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A Concise Synthesis of Novel Aryl Pyrimidine C ‐Nucleoside Analogs from Sugar Alkynes
Author(s) -
Zhang Fuyi,
Liang Yan,
Li Jing,
Gao Fei,
Liu Hong,
Zhao Yufen
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600583
Subject(s) - chemistry , pyrimidine , aryl , nucleoside , sugar , stereochemistry , nucleoside analogue , organic chemistry , combinatorial chemistry , alkyl
Aryl‐ and amino‐substituted pyrimidine C ‐nucleoside analogs have been synthesized in good to excellent yields by one‐pot coupling of terminal sugar alkynes, substituted benzoyl chlorides, and amidine salts. The reaction conditions are tolerant of various structurally complex sugars having sterically bulky groups, unprotected hydroxyl groups, and sensitive substituents. The sugar alkynes include structurally diverse pyranosides, acyclic glycosides, and furanosides. The substituted benzoyl chlorides bear electron‐withdrawing and ‐donating substituents with different steric hindrance. The amidine salts include acetamidine hydrochloride, benzamidine hydrochloride, and guanidine hydrochloride.